# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex1
_database_code_depnum_ccdc_archive 'CCDC 1824854'
loop_
_audit_author_name
_audit_author_address
'Adailton Bortoluzzi'
;Universidade Federal de Santa Catarina
Brazil
;
_audit_update_record             
;
2020-03-05 deposited with the CCDC.	2020-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 Mn N3 O3, Br, 0.5(H2 O)'
_chemical_formula_sum            'C15 H14 Br Mn N3 O3.50'
_chemical_formula_weight         427.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.6165(7)
_cell_length_b                   11.8250(3)
_cell_length_c                   14.9206(5)
_cell_angle_alpha                90
_cell_angle_beta                 117.8640(10)
_cell_angle_gamma                90
_cell_volume                     3371.74(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3187
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      28.63

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_F_000             1704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    3.173
_shelx_estimated_absorpt_T_min   0.395
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6140
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS 2014/4'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22881
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.025
_diffrn_reflns_theta_max         30.064
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4947
_reflns_number_gt                3823
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2018/1 (Sheldrick, 2018)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0234P)²+4.5407P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4947
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0690
_refine_ls_wR_factor_gt          0.0610
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.33768(2) 0.76638(2) 0.27004(2) 0.02174(7) Uani 1 1 d . . . . .
N1 N 0.40993(9) 0.87479(16) 0.37681(13) 0.0266(4) Uani 1 1 d . . . . .
C3 C 0.35365(11) 0.8218(2) 0.16940(16) 0.0348(5) Uani 1 1 d . . . . .
O3 O 0.36017(10) 0.85846(18) 0.10335(14) 0.0585(5) Uani 1 1 d . . . . .
C1 C 0.28287(11) 0.65908(18) 0.18253(15) 0.0295(4) Uani 1 1 d . . . . .
O1 O 0.24995(9) 0.59279(15) 0.12343(12) 0.0465(4) Uani 1 1 d . . . . .
C2 C 0.26119(11) 0.85497(17) 0.22743(16) 0.0288(4) Uani 1 1 d . . . . .
O2 O 0.21037(9) 0.90587(14) 0.19692(15) 0.0464(4) Uani 1 1 d . . . . .
C4 C 0.48135(11) 0.84048(18) 0.39701(17) 0.0322(5) Uani 1 1 d . . . . .
H4A H 0.515930 0.867051 0.465120 0.039 Uiso 1 1 calc R U . . .
H4B H 0.492764 0.875791 0.346377 0.039 Uiso 1 1 calc R U . . .
C5 C 0.48542(10) 0.71464(18) 0.39156(15) 0.0274(4) Uani 1 1 d . . . . .
N2 N 0.42477(8) 0.66338(14) 0.32934(12) 0.0246(3) Uani 1 1 d . . . . .
C9 C 0.42559(11) 0.55032(18) 0.31717(16) 0.0316(4) Uani 1 1 d . . . . .
H9 H 0.382989 0.513287 0.273666 0.038 Uiso 1 1 calc R U . . .
C8 C 0.48551(13) 0.4865(2) 0.36509(19) 0.0411(5) Uani 1 1 d . . . . .
H8 H 0.484457 0.407330 0.353473 0.049 Uiso 1 1 calc R U . . .
C7 C 0.54683(12) 0.5392(2) 0.42999(19) 0.0446(6) Uani 1 1 d . . . . .
H7 H 0.588670 0.496611 0.464897 0.054 Uiso 1 1 calc R U . . .
C6 C 0.54719(11) 0.6548(2) 0.44414(18) 0.0383(5) Uani 1 1 d . . . . .
H6 H 0.589102 0.692552 0.489155 0.046 Uiso 1 1 calc R U . . .
C10 C 0.40155(12) 0.87974(19) 0.46976(16) 0.0332(5) Uani 1 1 d . . . . .
H10A H 0.374615 0.948276 0.467721 0.040 Uiso 1 1 calc R U . . .
H10B H 0.448223 0.885383 0.529807 0.040 Uiso 1 1 calc R U . . .
C11 C 0.36453(10) 0.77742(17) 0.47966(14) 0.0251(4) Uani 1 1 d . . . . .
N3 N 0.32547(8) 0.71957(13) 0.39364(11) 0.0215(3) Uani 1 1 d . . . . .
C15 C 0.28400(10) 0.63616(16) 0.39596(15) 0.0260(4) Uani 1 1 d . . . . .
H15 H 0.254834 0.597423 0.334791 0.031 Uiso 1 1 calc R U . . .
C14 C 0.28210(12) 0.60460(19) 0.48361(17) 0.0327(5) Uani 1 1 d . . . . .
H14 H 0.252264 0.545151 0.482725 0.039 Uiso 1 1 calc R U . . .
C13 C 0.32421(12) 0.66071(19) 0.57257(17) 0.0363(5) Uani 1 1 d . . . . .
H13 H 0.324502 0.639490 0.634169 0.044 Uiso 1 1 calc R U . . .
C12 C 0.36591(11) 0.74808(19) 0.57084(15) 0.0328(5) Uani 1 1 d . . . . .
H12 H 0.395280 0.787802 0.631321 0.039 Uiso 1 1 calc R U . . .
Br1 Br 0.10459(2) 0.65242(2) 0.17880(2) 0.03448(7) Uani 1 1 d . . . . .
O1W O 0.500000 1.0255(2) 0.250000 0.0772(10) Uani 1 2 d S T P . .
H1W H 0.529400 1.073396 0.239800 0.093 Uiso 1 1 d R U . . .
H1 H 0.4047(12) 0.940(2) 0.3553(18) 0.033(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 C2 1.803(2) . y
Mn1 C1 1.809(2) . y
Mn1 C3 1.813(2) . y
Mn1 N3 2.0572(15) . y
Mn1 N2 2.0624(16) . y
Mn1 N1 2.0724(18) . y
N1 C10 1.481(3) . ?
N1 C4 1.485(3) . ?
N1 H1 0.83(3) . ?
C3 O3 1.144(3) . y
C1 O1 1.145(3) . y
C2 O2 1.144(2) . y
C4 C5 1.495(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N2 1.346(3) . ?
C5 C6 1.386(3) . ?
N2 C9 1.351(3) . ?
C9 C8 1.376(3) . ?
C9 H9 0.9500 . ?
C8 C7 1.372(4) . ?
C8 H8 0.9500 . ?
C7 C6 1.383(4) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C10 C11 1.496(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N3 1.347(2) . ?
C11 C12 1.391(3) . ?
N3 C15 1.344(2) . ?
C15 C14 1.379(3) . ?
C15 H15 0.9500 . ?
C14 C13 1.379(3) . ?
C14 H14 0.9500 . ?
C13 C12 1.379(3) . ?
C13 H13 0.9500 . ?
C12 H12 0.9500 . ?
O1W H1W 0.9154 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Mn1 C1 88.26(9) . . y
C2 Mn1 C3 89.78(9) . . y
C1 Mn1 C3 88.27(10) . . y
C2 Mn1 N3 89.53(8) . . y
C1 Mn1 N3 98.23(8) . . y
C3 Mn1 N3 173.44(9) . . y
C2 Mn1 N2 175.47(8) . . y
C1 Mn1 N2 93.10(8) . . y
C3 Mn1 N2 94.58(8) . . y
N3 Mn1 N2 86.00(6) . . y
C2 Mn1 N1 98.57(8) . . y
C1 Mn1 N1 173.10(8) . . y
C3 Mn1 N1 92.65(9) . . y
N3 Mn1 N1 81.00(7) . . y
N2 Mn1 N1 80.02(7) . . y
C10 N1 C4 113.04(17) . . ?
C10 N1 Mn1 111.48(13) . . ?
C4 N1 Mn1 109.00(13) . . ?
C10 N1 H1 105.8(16) . . ?
C4 N1 H1 106.0(16) . . ?
Mn1 N1 H1 111.4(17) . . ?
O3 C3 Mn1 176.5(2) . . y
O1 C1 Mn1 175.8(2) . . y
O2 C2 Mn1 175.9(2) . . y
N1 C4 C5 110.05(17) . . ?
N1 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
N1 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.2 . . ?
N2 C5 C6 122.1(2) . . ?
N2 C5 C4 115.01(17) . . ?
C6 C5 C4 122.9(2) . . ?
C5 N2 C9 117.96(18) . . ?
C5 N2 Mn1 115.45(13) . . ?
C9 N2 Mn1 126.43(14) . . ?
N2 C9 C8 122.8(2) . . ?
N2 C9 H9 118.6 . . ?
C8 C9 H9 118.6 . . ?
C7 C8 C9 118.8(2) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C8 C7 C6 119.4(2) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C6 C5 118.9(2) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
N1 C10 C11 111.45(17) . . ?
N1 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
N1 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
N3 C11 C12 121.51(19) . . ?
N3 C11 C10 116.27(17) . . ?
C12 C11 C10 122.05(18) . . ?
C15 N3 C11 118.45(17) . . ?
C15 N3 Mn1 125.95(13) . . ?
C11 N3 Mn1 115.57(13) . . ?
N3 C15 C14 122.61(19) . . ?
N3 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C13 C14 C15 118.9(2) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C14 C13 C12 119.06(19) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C12 C11 119.3(2) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C4 C5 89.5(2) . . . . ?
Mn1 N1 C4 C5 -35.09(19) . . . . ?
N1 C4 C5 N2 28.6(2) . . . . ?
N1 C4 C5 C6 -153.16(19) . . . . ?
C6 C5 N2 C9 -1.4(3) . . . . ?
C4 C5 N2 C9 176.83(17) . . . . ?
C6 C5 N2 Mn1 174.18(16) . . . . ?
C4 C5 N2 Mn1 -7.6(2) . . . . ?
C5 N2 C9 C8 -0.3(3) . . . . ?
Mn1 N2 C9 C8 -175.39(16) . . . . ?
N2 C9 C8 C7 1.6(3) . . . . ?
C9 C8 C7 C6 -1.2(4) . . . . ?
C8 C7 C6 C5 -0.5(4) . . . . ?
N2 C5 C6 C7 1.8(3) . . . . ?
C4 C5 C6 C7 -176.3(2) . . . . ?
C4 N1 C10 C11 -101.4(2) . . . . ?
Mn1 N1 C10 C11 21.8(2) . . . . ?
N1 C10 C11 N3 -21.3(3) . . . . ?
N1 C10 C11 C12 163.34(18) . . . . ?
C12 C11 N3 C15 4.0(3) . . . . ?
C10 C11 N3 C15 -171.35(17) . . . . ?
C12 C11 N3 Mn1 -174.41(15) . . . . ?
C10 C11 N3 Mn1 10.2(2) . . . . ?
C11 N3 C15 C14 -2.8(3) . . . . ?
Mn1 N3 C15 C14 175.49(14) . . . . ?
N3 C15 C14 C13 0.1(3) . . . . ?
C15 C14 C13 C12 1.2(3) . . . . ?
C14 C13 C12 C11 0.0(3) . . . . ?
N3 C11 C12 C13 -2.7(3) . . . . ?
C10 C11 C12 C13 172.42(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1W H1W Br1 0.92 2.39 3.2766(13) 162 3 yes
C4 H4B O1W 0.99 2.33 3.254(3) 155 . yes
N1 H1 Br1 0.83(3) 2.55(3) 3.3647(19) 170(2) 4 yes

_refine_diff_density_max         0.682
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.072

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Complex3
_database_code_depnum_ccdc_archive 'CCDC 1824855'
loop_
_audit_author_name
_audit_author_address
'Adailton Bortoluzzi'
;Universidade Federal de Santa Catarina
Brazil
;
_audit_update_record             
;
2020-03-05 deposited with the CCDC.	2020-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 Br Mn N3 O3'
_chemical_formula_sum            'C16 H15 Br Mn N3 O3'
_chemical_formula_weight         432.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.1164(8)
_cell_length_b                   7.3867(2)
_cell_length_c                   18.3010(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.9270(10)
_cell_angle_gamma                90
_cell_volume                     3441.04(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5233
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      29.34

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    3.108
_shelx_estimated_absorpt_T_min   0.401
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6251
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS 2014/4'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18246
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.600
_diffrn_reflns_theta_max         30.101
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5051
_reflns_number_gt                3891
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+4.2615P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5051
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.15648(2) 0.70281(4) 0.43169(2) 0.03148(9) Uani 1 1 d . . . . .
Mn1 Mn 0.15709(2) 0.54481(5) 0.30961(2) 0.02187(10) Uani 1 1 d . . . . .
O1 O 0.21593(9) 0.8503(3) 0.26435(12) 0.0448(5) Uani 1 1 d . . . . .
N1 N 0.12268(8) 0.3215(3) 0.35121(12) 0.0237(4) Uani 1 1 d . . . . .
N3 N 0.06517(9) 0.2476(3) 0.47639(13) 0.0325(5) Uani 1 1 d . . . . .
N2 N 0.22248(7) 0.4113(3) 0.36740(11) 0.0217(4) Uani 1 1 d . . . . .
C12 C 0.02726(10) 0.1824(4) 0.42057(15) 0.0280(5) Uani 1 1 d . . . . .
C2 C 0.09731(11) 0.6622(4) 0.26713(16) 0.0349(6) Uani 1 1 d . . . . .
O2 O 0.06060(10) 0.7432(4) 0.23896(15) 0.0595(7) Uani 1 1 d . . . . .
C1 C 0.19351(11) 0.7303(4) 0.28183(14) 0.0298(6) Uani 1 1 d . . . . .
C4 C 0.15992(10) 0.1683(4) 0.35676(16) 0.0296(6) Uani 1 1 d . . . . .
H6 H 0.155592 0.108829 0.307273 0.036 Uiso 1 1 calc R U . . .
H7 H 0.152485 0.077820 0.392919 0.036 Uiso 1 1 calc R U . . .
C5 C 0.21511(9) 0.2363(3) 0.38216(13) 0.0224(5) Uani 1 1 d . . . . .
C9 C 0.27065(9) 0.4828(4) 0.39152(14) 0.0264(5) Uani 1 1 d . . . . .
H5 H 0.275795 0.607730 0.383089 0.032 Uiso 1 1 calc R U . . .
C8 C 0.31280(10) 0.3805(4) 0.42809(14) 0.0307(6) Uani 1 1 d . . . . .
H4 H 0.346428 0.434540 0.444396 0.037 Uiso 1 1 calc R U . . .
C7 C 0.30576(10) 0.1996(4) 0.44079(14) 0.0300(6) Uani 1 1 d . . . . .
H3 H 0.334633 0.126373 0.464489 0.036 Uiso 1 1 calc R U . . .
C6 C 0.25596(10) 0.1257(4) 0.41851(14) 0.0268(5) Uani 1 1 d . . . . .
H2 H 0.249856 0.001987 0.427898 0.032 Uiso 1 1 calc R U . . .
C10 C 0.06890(10) 0.2658(4) 0.31215(15) 0.0305(6) Uani 1 1 d . . . . .
H15 H 0.070033 0.222576 0.261326 0.037 Uiso 1 1 calc R U . . .
H14 H 0.045794 0.373552 0.306176 0.037 Uiso 1 1 calc R U . . .
C11 C 0.04428(10) 0.1171(4) 0.35187(15) 0.0320(6) Uani 1 1 d . . . . .
H12 H 0.013409 0.066533 0.316200 0.038 Uiso 1 1 calc R U . . .
H13 H 0.070108 0.018136 0.366420 0.038 Uiso 1 1 calc R U . . .
C16 C 0.05108(13) 0.3020(4) 0.53860(17) 0.0404(7) Uani 1 1 d . . . . .
H11 H 0.077574 0.347705 0.578630 0.049 Uiso 1 1 calc R U . . .
C15 C -0.00012(14) 0.2955(5) 0.5480(2) 0.0462(8) Uani 1 1 d . . . . .
H8 H -0.008249 0.333563 0.593736 0.055 Uiso 1 1 calc R U . . .
C14 C -0.03904(13) 0.2326(5) 0.4896(2) 0.0481(8) Uani 1 1 d . . . . .
H10 H -0.074633 0.228605 0.493746 0.058 Uiso 1 1 calc R U . . .
C13 C -0.02515(10) 0.1761(4) 0.42541(18) 0.0367(7) Uani 1 1 d . . . . .
H9 H -0.051204 0.132651 0.384318 0.044 Uiso 1 1 calc R U . . .
C3 C 0.15626(9) 0.4285(4) 0.21990(16) 0.0286(6) Uani 1 1 d . . . . .
O3 O 0.15503(9) 0.3657(3) 0.16748(13) 0.0451(5) Uani 1 1 d . . . . .
H1 H 0.1191(11) 0.349(4) 0.3955(17) 0.025(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Mn1 2.5238(4) . ?
Mn1 C2 1.803(3) . ?
Mn1 C1 1.805(3) . ?
Mn1 C3 1.849(3) . ?
Mn1 N2 2.049(2) . ?
Mn1 N1 2.101(2) . ?
O1 C1 1.146(3) . ?
N1 C4 1.481(3) . ?
N1 C10 1.485(3) . ?
N1 H1 0.86(3) . ?
N3 C16 1.334(4) . ?
N3 C12 1.343(4) . ?
N2 C5 1.343(3) . ?
N2 C9 1.345(3) . ?
C12 C13 1.392(4) . ?
C12 C11 1.504(4) . ?
C2 O2 1.150(4) . ?
C4 C5 1.499(3) . ?
C4 H6 0.9900 . ?
C4 H7 0.9900 . ?
C5 C6 1.389(3) . ?
C9 C8 1.379(4) . ?
C9 H5 0.9500 . ?
C8 C7 1.376(4) . ?
C8 H4 0.9500 . ?
C7 C6 1.385(4) . ?
C7 H3 0.9500 . ?
C6 H2 0.9500 . ?
C10 C11 1.535(4) . ?
C10 H15 0.9900 . ?
C10 H14 0.9900 . ?
C11 H12 0.9900 . ?
C11 H13 0.9900 . ?
C16 C15 1.387(5) . ?
C16 H11 0.9500 . ?
C15 C14 1.381(5) . ?
C15 H8 0.9500 . ?
C14 C13 1.369(5) . ?
C14 H10 0.9500 . ?
C13 H9 0.9500 . ?
C3 O3 1.060(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Mn1 C1 88.48(13) . . ?
C2 Mn1 C3 90.20(12) . . ?
C1 Mn1 C3 90.27(11) . . ?
C2 Mn1 N2 174.42(10) . . ?
C1 Mn1 N2 94.59(10) . . ?
C3 Mn1 N2 94.44(9) . . ?
C2 Mn1 N1 97.73(11) . . ?
C1 Mn1 N1 173.35(10) . . ?
C3 Mn1 N1 92.07(10) . . ?
N2 Mn1 N1 79.03(8) . . ?
C2 Mn1 Br1 89.03(9) . . ?
C1 Mn1 Br1 90.37(8) . . ?
C3 Mn1 Br1 178.98(8) . . ?
N2 Mn1 Br1 86.29(6) . . ?
N1 Mn1 Br1 87.39(6) . . ?
C4 N1 C10 110.9(2) . . ?
C4 N1 Mn1 107.28(15) . . ?
C10 N1 Mn1 118.58(16) . . ?
C4 N1 H1 109(2) . . ?
C10 N1 H1 103(2) . . ?
Mn1 N1 H1 108(2) . . ?
C16 N3 C12 117.4(2) . . ?
C5 N2 C9 118.5(2) . . ?
C5 N2 Mn1 115.26(15) . . ?
C9 N2 Mn1 126.20(18) . . ?
N3 C12 C13 122.1(3) . . ?
N3 C12 C11 116.5(2) . . ?
C13 C12 C11 121.4(3) . . ?
O2 C2 Mn1 176.8(3) . . ?
O1 C1 Mn1 178.8(3) . . ?
N1 C4 C5 109.7(2) . . ?
N1 C4 H6 109.7 . . ?
C5 C4 H6 109.7 . . ?
N1 C4 H7 109.7 . . ?
C5 C4 H7 109.7 . . ?
H6 C4 H7 108.2 . . ?
N2 C5 C6 122.2(2) . . ?
N2 C5 C4 115.5(2) . . ?
C6 C5 C4 122.3(2) . . ?
N2 C9 C8 122.0(3) . . ?
N2 C9 H5 119.0 . . ?
C8 C9 H5 119.0 . . ?
C7 C8 C9 119.5(2) . . ?
C7 C8 H4 120.3 . . ?
C9 C8 H4 120.3 . . ?
C8 C7 C6 119.0(2) . . ?
C8 C7 H3 120.5 . . ?
C6 C7 H3 120.5 . . ?
C7 C6 C5 118.7(3) . . ?
C7 C6 H2 120.7 . . ?
C5 C6 H2 120.7 . . ?
N1 C10 C11 114.9(2) . . ?
N1 C10 H15 108.5 . . ?
C11 C10 H15 108.5 . . ?
N1 C10 H14 108.5 . . ?
C11 C10 H14 108.5 . . ?
H15 C10 H14 107.5 . . ?
C12 C11 C10 113.6(2) . . ?
C12 C11 H12 108.9 . . ?
C10 C11 H12 108.9 . . ?
C12 C11 H13 108.9 . . ?
C10 C11 H13 108.9 . . ?
H12 C11 H13 107.7 . . ?
N3 C16 C15 123.6(3) . . ?
N3 C16 H11 118.2 . . ?
C15 C16 H11 118.2 . . ?
C14 C15 C16 118.5(3) . . ?
C14 C15 H8 120.7 . . ?
C16 C15 H8 120.7 . . ?
C13 C14 C15 118.5(3) . . ?
C13 C14 H10 120.8 . . ?
C15 C14 H10 120.8 . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H9 120.1 . . ?
C12 C13 H9 120.1 . . ?
O3 C3 Mn1 178.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N3 C12 C13 2.0(4) . . . . ?
C16 N3 C12 C11 -178.3(3) . . . . ?
C10 N1 C4 C5 168.8(2) . . . . ?
Mn1 N1 C4 C5 37.8(2) . . . . ?
C9 N2 C5 C6 -2.8(3) . . . . ?
Mn1 N2 C5 C6 177.67(18) . . . . ?
C9 N2 C5 C4 177.2(2) . . . . ?
Mn1 N2 C5 C4 -2.3(3) . . . . ?
N1 C4 C5 N2 -24.5(3) . . . . ?
N1 C4 C5 C6 155.5(2) . . . . ?
C5 N2 C9 C8 2.6(3) . . . . ?
Mn1 N2 C9 C8 -177.95(18) . . . . ?
N2 C9 C8 C7 -0.2(4) . . . . ?
C9 C8 C7 C6 -2.0(4) . . . . ?
C8 C7 C6 C5 1.8(4) . . . . ?
N2 C5 C6 C7 0.6(4) . . . . ?
C4 C5 C6 C7 -179.4(2) . . . . ?
C4 N1 C10 C11 62.5(3) . . . . ?
Mn1 N1 C10 C11 -172.73(19) . . . . ?
N3 C12 C11 C10 -61.6(3) . . . . ?
C13 C12 C11 C10 118.0(3) . . . . ?
N1 C10 C11 C12 73.5(3) . . . . ?
C12 N3 C16 C15 -0.4(5) . . . . ?
N3 C16 C15 C14 -1.2(5) . . . . ?
C16 C15 C14 C13 1.3(5) . . . . ?
C15 C14 C13 C12 0.2(5) . . . . ?
N3 C12 C13 C14 -2.0(4) . . . . ?
C11 C12 C13 C14 178.4(3) . . . . ?

_refine_diff_density_max         0.636
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.094

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex4
_database_code_depnum_ccdc_archive 'CCDC 1824856'
loop_
_audit_author_name
_audit_author_address
'Adailton Bortoluzzi'
;Universidade Federal de Santa Catarina
Brazil
;
_audit_update_record             
;
2020-03-05 deposited with the CCDC.	2020-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 Br Mn N3 O3'
_chemical_formula_sum            'C17 H17 Br Mn N3 O3'
_chemical_formula_weight         446.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0271(4)
_cell_length_b                   9.3057(5)
_cell_length_c                   12.9921(7)
_cell_angle_alpha                87.029(2)
_cell_angle_beta                 89.037(2)
_cell_angle_gamma                67.346(2)
_cell_volume                     894.40(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2323
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      28.29

_exptl_crystal_description       Fragment
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.992
_shelx_estimated_absorpt_T_min   0.467
_shelx_estimated_absorpt_T_max   0.841
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4672
_exptl_absorpt_correction_T_max  0.8409
_exptl_absorpt_process_details   
;
Bruker APEX2, SAINT and SADABS, version 2011.8-0; Bruker AXS Inc., 
Madison, Wisconsin, USA
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15466
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.374
_diffrn_reflns_theta_max         28.373
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4475
_reflns_number_gt                3754
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0234P)²+0.3887P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4475
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0235
_refine_ls_wR_factor_ref         0.0564
_refine_ls_wR_factor_gt          0.0530
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.60682(3) 0.18596(3) 0.70883(2) 0.02399(7) Uani 1 1 d . . . . .
Br1 Br 0.30622(2) 0.26751(2) 0.61785(2) 0.03426(6) Uani 1 1 d . . . . .
C1 C 0.4978(3) 0.1700(2) 0.82960(16) 0.0389(4) Uani 1 1 d . . . . .
O1 O 0.4347(2) 0.1496(2) 0.90597(13) 0.0634(5) Uani 1 1 d . . . . .
C2 C 0.6449(2) -0.0168(2) 0.69807(14) 0.0323(4) Uani 1 1 d . . . . .
O2 O 0.6661(2) -0.14595(16) 0.69806(12) 0.0478(4) Uani 1 1 d . . . . .
C3 C 0.8216(3) 0.1313(2) 0.77230(13) 0.0301(4) Uani 1 1 d . . . . .
O3 O 0.95610(19) 0.09503(17) 0.81269(11) 0.0426(3) Uani 1 1 d . . . . .
N1 N 0.53840(19) 0.42784(17) 0.72716(11) 0.0244(3) Uani 1 1 d . . . . .
C11 C 0.5948(2) 0.51098(19) 0.64218(13) 0.0272(3) Uani 1 1 d . . . . .
H11A H 0.5810 0.6152 0.6642 0.033 Uiso 1 1 calc R U . . .
H11B H 0.5147 0.5262 0.5820 0.033 Uiso 1 1 calc R U . . .
C12 C 0.7896(2) 0.4227(2) 0.61019(14) 0.0275(4) Uani 1 1 d . . . . .
H12A H 0.8374 0.4967 0.5764 0.033 Uiso 1 1 calc R U . . .
H12B H 0.8639 0.3746 0.6723 0.033 Uiso 1 1 calc R U . . .
C13 C 0.8047(2) 0.29768(18) 0.53732(13) 0.0228(3) Uani 1 1 d . . . . .
N14 N 0.72109(17) 0.19949(15) 0.56287(10) 0.0222(3) Uani 1 1 d . . . . .
C15 C 0.7211(2) 0.0979(2) 0.49223(13) 0.0273(3) Uani 1 1 d . . . . .
H15 H 0.6603 0.0300 0.5087 0.033 Uiso 1 1 calc R U . . .
C16 C 0.8042(2) 0.0871(2) 0.39798(14) 0.0299(4) Uani 1 1 d . . . . .
H16 H 0.8003 0.0137 0.3509 0.036 Uiso 1 1 calc R U . . .
C17 C 0.8930(2) 0.1846(2) 0.37293(14) 0.0304(4) Uani 1 1 d . . . . .
H17 H 0.9535 0.1786 0.3088 0.037 Uiso 1 1 calc R U . . .
C18 C 0.8920(2) 0.2911(2) 0.44320(14) 0.0279(4) Uani 1 1 d . . . . .
H18 H 0.9513 0.3603 0.4273 0.033 Uiso 1 1 calc R U . . .
C21 C 0.5817(2) 0.4708(2) 0.82961(14) 0.0325(4) Uani 1 1 d . . . . .
H21A H 0.7076 0.4645 0.8283 0.039 Uiso 1 1 calc R U . . .
H21B H 0.5747 0.3931 0.8827 0.039 Uiso 1 1 calc R U . . .
C22 C 0.4578(3) 0.6334(2) 0.86125(15) 0.0353(4) Uani 1 1 d . . . . .
H22A H 0.5091 0.6588 0.9232 0.042 Uiso 1 1 calc R U . . .
H22B H 0.4556 0.7103 0.8052 0.042 Uiso 1 1 calc R U . . .
C23 C 0.2666(2) 0.6496(2) 0.88417(13) 0.0291(4) Uani 1 1 d . . . . .
N24 N 0.2105(2) 0.5499(2) 0.84040(14) 0.0441(4) Uani 1 1 d . . . . .
C25 C 0.0398(3) 0.5644(3) 0.85655(19) 0.0547(6) Uani 1 1 d . . . . .
H25 H -0.0010 0.4941 0.8248 0.066 Uiso 1 1 calc R U . . .
C26 C -0.0793(3) 0.6748(3) 0.91629(18) 0.0515(6) Uani 1 1 d . . . . .
H26 H -0.1996 0.6813 0.9254 0.062 Uiso 1 1 calc R U . . .
C27 C -0.0207(3) 0.7759(3) 0.96271(17) 0.0480(5) Uani 1 1 d . . . . .
H27 H -0.0992 0.8531 1.0054 0.058 Uiso 1 1 calc R U . . .
C28 C 0.1550(3) 0.7632(2) 0.94617(15) 0.0380(4) Uani 1 1 d . . . . .
H28 H 0.1984 0.8323 0.9773 0.046 Uiso 1 1 calc R U . . .
H1N H 0.426(3) 0.457(2) 0.7271(15) 0.032(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 C3 1.8002(19) . y
Mn1 C2 1.8044(19) . y
Mn1 C1 1.811(2) . y
Mn1 N14 2.1117(13) . y
Mn1 N1 2.1269(14) . y
Mn1 Br1 2.5273(3) . y
C1 O1 1.147(2) . y
C2 O2 1.147(2) . y
C3 O3 1.129(2) . y
N1 C11 1.479(2) . ?
N1 C21 1.493(2) . ?
N1 H1N 0.83(2) . ?
C11 C12 1.522(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.505(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N14 1.352(2) . ?
C13 C18 1.392(2) . ?
N14 C15 1.351(2) . ?
C15 C16 1.374(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.377(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C21 C22 1.529(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.509(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 N24 1.332(2) . ?
C23 C28 1.380(3) . ?
N24 C25 1.338(3) . ?
C25 C26 1.369(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.371(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.383(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 Mn1 C2 90.32(8) . . y
C3 Mn1 C1 91.41(9) . . y
C2 Mn1 C1 85.25(9) . . y
C3 Mn1 N14 91.95(6) . . y
C2 Mn1 N14 92.58(7) . . y
C1 Mn1 N14 176.01(8) . . y
C3 Mn1 N1 93.06(7) . . y
C2 Mn1 N1 174.76(7) . . y
C1 Mn1 N1 90.66(7) . . y
N14 Mn1 N1 91.30(5) . . y
C3 Mn1 Br1 178.81(6) . . y
C2 Mn1 Br1 90.64(6) . . y
C1 Mn1 Br1 89.37(7) . . y
N14 Mn1 Br1 87.30(4) . . y
N1 Mn1 Br1 86.03(4) . . y
O1 C1 Mn1 175.59(19) . . y
O2 C2 Mn1 175.43(17) . . y
O3 C3 Mn1 178.99(17) . . y
C11 N1 C21 111.13(13) . . ?
C11 N1 Mn1 115.45(10) . . ?
C21 N1 Mn1 115.98(11) . . ?
C11 N1 H1N 109.9(14) . . ?
C21 N1 H1N 104.4(13) . . ?
Mn1 N1 H1N 98.4(14) . . ?
N1 C11 C12 112.25(14) . . ?
N1 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 111.47(13) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N14 C13 C18 121.26(15) . . ?
N14 C13 C12 118.20(14) . . ?
C18 C13 C12 120.39(14) . . ?
C15 N14 C13 117.41(14) . . ?
C15 N14 Mn1 118.47(11) . . ?
C13 N14 Mn1 124.00(11) . . ?
N14 C15 C16 123.70(15) . . ?
N14 C15 H15 118.2 . . ?
C16 C15 H15 118.2 . . ?
C15 C16 C17 118.91(16) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C16 C17 C18 118.36(16) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C17 C18 C13 120.35(15) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
N1 C21 C22 114.56(15) . . ?
N1 C21 H21A 108.6 . . ?
C22 C21 H21A 108.6 . . ?
N1 C21 H21B 108.6 . . ?
C22 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
C23 C22 C21 113.90(15) . . ?
C23 C22 H22A 108.8 . . ?
C21 C22 H22A 108.8 . . ?
C23 C22 H22B 108.8 . . ?
C21 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
N24 C23 C28 121.70(17) . . ?
N24 C23 C22 116.53(15) . . ?
C28 C23 C22 121.76(16) . . ?
C23 N24 C25 118.00(17) . . ?
N24 C25 C26 123.7(2) . . ?
N24 C25 H25 118.2 . . ?
C26 C25 H25 118.2 . . ?
C25 C26 C27 118.3(2) . . ?
C25 C26 H26 120.8 . . ?
C27 C26 H26 120.8 . . ?
C26 C27 C28 118.72(19) . . ?
C26 C27 H27 120.6 . . ?
C28 C27 H27 120.6 . . ?
C23 C28 C27 119.56(19) . . ?
C23 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 N1 C11 C12 87.95(17) . . . . ?
Mn1 N1 C11 C12 -46.80(16) . . . . ?
N1 C11 C12 C13 82.32(18) . . . . ?
C11 C12 C13 N14 -48.8(2) . . . . ?
C11 C12 C13 C18 126.88(16) . . . . ?
C18 C13 N14 C15 -1.9(2) . . . . ?
C12 C13 N14 C15 173.75(14) . . . . ?
C18 C13 N14 Mn1 173.92(12) . . . . ?
C12 C13 N14 Mn1 -10.4(2) . . . . ?
C13 N14 C15 C16 1.5(2) . . . . ?
Mn1 N14 C15 C16 -174.58(13) . . . . ?
N14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C18 -1.1(3) . . . . ?
C16 C17 C18 C13 0.7(3) . . . . ?
N14 C13 C18 C17 0.8(3) . . . . ?
C12 C13 C18 C17 -174.71(16) . . . . ?
C11 N1 C21 C22 74.13(18) . . . . ?
Mn1 N1 C21 C22 -151.39(12) . . . . ?
N1 C21 C22 C23 68.5(2) . . . . ?
C21 C22 C23 N24 -23.8(2) . . . . ?
C21 C22 C23 C28 157.05(18) . . . . ?
C28 C23 N24 C25 1.3(3) . . . . ?
C22 C23 N24 C25 -177.9(2) . . . . ?
C23 N24 C25 C26 -0.7(4) . . . . ?
N24 C25 C26 C27 -0.3(4) . . . . ?
C25 C26 C27 C28 0.8(4) . . . . ?
N24 C23 C28 C27 -0.8(3) . . . . ?
C22 C23 C28 C27 178.35(19) . . . . ?
C26 C27 C28 C23 -0.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N N24 0.83(2) 2.19(2) 2.850(2) 135.7(17) .
N1 H1N Br1 0.83(2) 2.77(2) 3.1885(14) 113.2(16) .

_refine_diff_density_max         0.326
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.054

